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Organic Reaction Attackers: Nucleophiles, Electrophiles, and Free Radicals

Learn about the key characters in organic reactions - nucleophiles, electrophiles, and free radicals - and how they interact with different types of bonds. Understand what influences each attacker and the reactions they initiate. Discover the mechanisms behind free radical substitution, electrophilic addition, and nucleophilic substitution reactions in organic chemistry.

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Organic Reaction Attackers: Nucleophiles, Electrophiles, and Free Radicals

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  1. SOME IMPORTANT CHARACTERS FOR ORGANIC REACTIONS MECHANISMS Dr Seemal Jlani Chem-240

  2. MEET THE ATTACKERS Dr Seemal Jlani Chem-240 Press the space bar

  3. MEET THE ATTACKERS I AM A NUCLEOPHILE I HAVE A LONE PAIR WHICH I CAN USE TO FORM A NEW BOND. I ATTACK ELECTRON DEFICIENT AREAS (those with a + ord+) Dr Seemal Jlani Chem-240

  4. MEET THE ATTACKERS Dr Seemal Jlani Chem-240 Press the space bar

  5. MEET THE ATTACKERS I AM AN ELECTROPHILE I HAVE A + CHARGE or ad+ CHARGE. I ATTACK ELECTRON RICH AREAS SUCH AS C=C DOUBLE BONDS. Dr Seemal Jlani Chem-240

  6. MEET THE ATTACKERS Dr Seemal Jlani Chem-240 Press the space bar

  7. MEET THE ATTACKERS AND I AM A FREE RADICAL I HAVE AN UNPAIRED ELECTRON WHICH I WANT TO PAIR UP. I AM VERY REACTIVE AND DON’T MIND WHERE I ATTACK… WATCH OUT! Dr Seemal Jlani Chem-240

  8. WHO IS ATTACKED? THE BONDING IN A MOLECULE INFLUENCES WHAT WILL ATTACK IT Dr Seemal Jlani Chem-240

  9. WHO IS ATTACKED? THE BONDING IN A MOLECULE INFLUENCES WHAT WILL ATTACK IT SINGLE A typical covalent bond with one shared pair – nothing to tempt an attacking species Dr Seemal Jlani Chem-240

  10. WHO IS ATTACKED? THE BONDING IN A MOLECULE INFLUENCES WHAT WILL ATTACK IT SINGLE MULTIPLE A typical covalent bond with one shared pair – nothing to tempt an attacking species Bond has twice as many electrons – species which like electrons will be attracted Dr Seemal Jlani Chem-240

  11. WHO IS ATTACKED? THE BONDING IN A MOLECULE INFLUENCES WHAT WILL ATTACK IT SINGLE MULTIPLE NON-POLAR A typical covalent bond with one shared pair – nothing to tempt an attacking species Bond has twice as many electrons – species which like electrons will be attracted Similar atoms have an equal attraction for the shared pair of the covalent bond Dr Seemal Jlani Chem-240

  12. WHO IS ATTACKED? THE BONDING IN A MOLECULE INFLUENCES WHAT WILL ATTACK IT SINGLE MULTIPLE NON-POLAR POLAR A typical covalent bond with one shared pair – nothing to tempt an attacking species Bond has twice as many electrons – species which like electrons will be attracted Similar atoms have an equal attraction for the shared pair of the covalent bond d+ d- Atoms have different electronegativities and the shared pair will be attracted more to one end – species known as nucleophiles will be attracted to the slightly positive end Dr Seemal Jlani Chem-240

  13. WHO IS ATTACKED? THE BONDING IN A MOLECULE INFLUENCES WHAT WILL ATTACK IT SINGLE MULTIPLE NON-POLAR POLAR A typical covalent bond with one shared pair – nothing to tempt an attacking species Bond has twice as many electrons – species which like electrons will be attracted Similar atoms have an equal attraction for the shared pair of the covalent bond d+ d- Atoms have different electronegativities and the shared pair will be attracted more to one end – species known as nucleophiles will be attracted to the slightly positive end Dr Seemal Jlani Chem-240

  14. WHAT ATTACKS ALKANES? ALKANES ARE RELATIVELY UNREACTIVE ORGANIC COMPOUNDS ALKANES CONTAIN TWO BOND TYPES C-H and C-C Both bonds are single – no electron rich areas Bonds are non-polar - no electron deficient areas Free radicals are very reactive and do attack FREE RADICAL SUBSTITUTION Dr Seemal Jlani Chem-240

  15. WHAT ATTACKS ALKENES? ALKENES ARE MUCH MORE REACTIVE THAN ALKANES ALKENES CONTAIN A C=C BOND There will be twice as many electrons between the carbon atoms as there are in a single bond C=C bond is double – an electron rich area Bonds are non-polar - no electron deficient areas ELECTROPHILIC ADDITION Dr Seemal Jlani Chem-240

  16. WHAT ATTACKS HALOGENOALKENES? HALOGENOALKANES ARE MUCH MORE REACTIVE THAN ALKANES HALOGENOALKANES CONTAIN A POLAR BOND The halogen is more electronegative than the carbon attracts the shared electron pair. d+ d- Bond is single – not an electron rich area Bond is polar – the greater electronegativity of the halogen creates a dipole making the carbon atom electron deficient. NUCLEOPHILIC SUBSTITUTION Dr Seemal Jlani Chem-240

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